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Volumn , Issue 19, 2007, Pages 2957-2966

β-Oxo amides: Inexpensive and efficient ligands for the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction

Author keywords

Oxo amide; Aryl halides; Arylboronic acids; Palladium(II) acetate; Suzuki Miyaura cross coupling reaction

Indexed keywords

ARYL HALIDES; ARYLBORONIC ACIDS; PALLADIUM(II) ACETATE; SUZUKI-MIYAURA CROSS-COUPLING REACTION;

EID: 35348955983     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983891     Document Type: Article
Times cited : (16)

References (85)
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    • For selected representative papers on palladium/phosphine-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
    • For selected representative papers on palladium/phosphine-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
  • 25
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    • For representative papers on palladium/carbene-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Gstottmayr, C. W. K.; Bohm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. Angew. Chem. Int. Ed. 2002, 41, 1363.
    • For representative papers on palladium/carbene-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Gstottmayr, C. W. K.; Bohm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. Angew. Chem. Int. Ed. 2002, 41, 1363.
  • 29
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    • For representative papers on palladium/oxazoline-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2002, 43, 4955.
    • For representative papers on palladium/oxazoline-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2002, 43, 4955.
  • 34
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    • For representative papers on palladium/amine-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2003, 44, 7993.
    • For representative papers on palladium/amine-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2003, 44, 7993.
  • 41
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    • For representative papers on palladium/amino acid-catalyzed Suzuki-Miyaura cross-couplings, see: Cui, X.; Tian, Q.; Wang, J.-R.; Liu, L.; Guo, Q.-X. Synthesis 2007, 393.
    • For representative papers on palladium/amino acid-catalyzed Suzuki-Miyaura cross-couplings, see: Cui, X.; Tian, Q.; Wang, J.-R.; Liu, L.; Guo, Q.-X. Synthesis 2007, 393.
  • 42
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    • For representative papers on palladium/heterocycle-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Mathews, C. J.; Smith, P. J.; Welton, T. J. Mol. Catal. A: Chem. 2004, 214, 27.
    • For representative papers on palladium/heterocycle-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Mathews, C. J.; Smith, P. J.; Welton, T. J. Mol. Catal. A: Chem. 2004, 214, 27.
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    • Pyrimidines: (i) Li, J.-H.; Zhang, X.-D.; Xie, Y.-X. Synlett 2005, 1897.
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    • For a representative paper on palladium/diazabutadiene-catalyzed Suzuki-Miyaura cross-couplings, see: Grasa, G. A.; Hillier, A. C.; Nolan, S. P. Org. Lett. 2001, 3, 1077.
    • For a representative paper on palladium/diazabutadiene-catalyzed Suzuki-Miyaura cross-couplings, see: Grasa, G. A.; Hillier, A. C.; Nolan, S. P. Org. Lett. 2001, 3, 1077.
  • 52
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    • For representative papers on palladium/urea-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Dai, M. J.; Liang, B.; Wang, C. H.; You, Z. J.; Xiang, J.; Dong, G. B.; Chen, J. H.; Yang, Z. Adv. Synth. Catal. 2004, 346, 1669.
    • For representative papers on palladium/urea-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Dai, M. J.; Liang, B.; Wang, C. H.; You, Z. J.; Xiang, J.; Dong, G. B.; Chen, J. H.; Yang, Z. Adv. Synth. Catal. 2004, 346, 1669.
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    • For representative papers on palladium/guanidine-catalyzed Suzuki-Miyaura cross-couplings, see: Li, S.; Lin, Y.; Cao, J.; Zhang, S. J. Org. Chem. 2007, 72, 4067.
    • For representative papers on palladium/guanidine-catalyzed Suzuki-Miyaura cross-couplings, see: Li, S.; Lin, Y.; Cao, J.; Zhang, S. J. Org. Chem. 2007, 72, 4067.
  • 56
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    • For representative papers on palladium/hydrazone-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Mino, T.; Shirae, Y.; Sakamoto, M.; Fujita, T. Synlett 2003, 882.
    • For representative papers on palladium/hydrazone-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Mino, T.; Shirae, Y.; Sakamoto, M.; Fujita, T. Synlett 2003, 882.
  • 58
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    • For representative papers on palladium/surfactant-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Bhattacharya, S.; Srivastava, A.; Sengupta, S. Tetrahedron Lett. 2005, 46, 3557.
    • For representative papers on palladium/surfactant-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Bhattacharya, S.; Srivastava, A.; Sengupta, S. Tetrahedron Lett. 2005, 46, 3557.
  • 61
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    • For selected representative papers on palladium/the other ligand-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Chen, M.-T, Huang, C.-A, Chen, C.-T. Eur. J. Inorg. Chem. 2006, 4642
    • For selected representative papers on palladium/the other ligand-catalyzed Suzuki-Miyaura cross-couplings, see: (a) Chen, M.-T.; Huang, C.-A.; Chen, C.-T. Eur. J. Inorg. Chem. 2006, 4642.
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    • For selected representative papers on ligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings see: (a) Deng, Y, Gong, L, Mi, A, Liu, H, Jiang, Y. Synthesis 2003, 337
    • For selected representative papers on ligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings see: (a) Deng, Y.; Gong, L.; Mi, A.; Liu, H.; Jiang, Y. Synthesis 2003, 337.
  • 76
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    • According to the previous and present results, three roles of TBAB may play in the reaction: (i) activation of the active Pd(0) species with the formation of anionic species, (ii) stabilization of the low coordinate Pd(0) species, (iii) phase-transfer catalyst for the inorganic base/solvent/substrate/ product phases. For representative papers on TBAB-improved Suzuki reactions, see: (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170.
    • According to the previous and present results, three roles of TBAB may play in the reaction: (i) activation of the active Pd(0) species with the formation of anionic species, (ii) stabilization of the low coordinate Pd(0) species, (iii) phase-transfer catalyst for the inorganic base/solvent/substrate/ product phases. For representative papers on TBAB-improved Suzuki reactions, see: (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170.
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    • and references cited therein
    • (c) Lysén, M.; Köhler, K. Synlett 2005, 1671; and references cited therein.
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    • Lysén, M.1    Köhler, K.2


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